Radical-based route to 2-(trifluoromethyl)-1,3,4-oxadiazoles and trifluoromethyl-substituted polycyclic 1,2,4-triazoles and dihydrofurans.

Ling Qin; Samir Z Zard

doi:10.1021/acs.orglett.5b00457

Radical-based route to 2-(trifluoromethyl)-1,3,4-oxadiazoles and trifluoromethyl-substituted polycyclic 1,2,4-triazoles and dihydrofurans.

Ling Qin ¹ Samir Z Zard ¹

1 DCSO - Laboratoire de synthèse organique

Abstract : O-Ethyl S-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]methyl xanthate was readily prepared on a large scale and shown to undergo very efficient intermolecular radical additions to unactivated alkenes. The products were further elaborated by exploiting both radical and ionic processes to provide a variety of trifluoromethyl-substituted derivatives, including medicinally relevant triazoles. In particular, the application of a radical allylation on the initial adducts leads to structures that are able to undergo intramolecular [4 + 2] cycloaddition reactions.

Type de document :

Article dans une revue

Organic Letters, American Chemical Society, 2015, 17 (6), pp.1577-80. 〈10.1021/acs.orglett.5b00457〉

Domaine :

Chimie / Chimie organique

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https://hal-polytechnique.archives-ouvertes.fr/hal-01152227
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Soumis le : vendredi 15 mai 2015 - 15:45:23
Dernière modification le : jeudi 10 mai 2018 - 02:07:45

Radical-based route to 2-(trifluoromethyl)-1,3,4-oxadiazoles and trifluoromethyl-substituted polycyclic 1,2,4-triazoles and dihydrofurans.

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Radical-based route to 2-(trifluoromethyl)-1,3,4-oxadiazoles and trifluoromethyl-substituted polycyclic 1,2,4-triazoles and dihydrofurans.

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